All In, All Out: An Entrepreneur’s Journey

It’s been a 33 year journey, but I’ll skip the super early stuff.

In 2008, I was a top sales producer at ADP, selling software and services to small businesses in Phoenix. I was there for about one year.

I left there and went to do the same thing at a “mom & pop” payroll provider in Monroe, LA. That was where the entrepreneurial seed was planted; we only had 10 employees and I got to see how the entire business was run. More importantly, I recognized how important technology was for us and our customers.

Once I learned the business inside and out, I went on to sell software to payroll companies, accounting firms and banks all over the country.

I built up enough courage to start my own payroll company. Kind of. It was more of an “intrepreneur” role. I still had a bit of a security blanket.

You see, I convinced a credit card processor to give me $400k to start a payroll company for them as a subsidiary, and provide me with $100k salary with growth bonuses. And we grew the heck out of that thing. It’s still thriving today as Alpha Payroll Services.

But something was still missing.

Fast forward to a few years later, in 2012 — I was introduced to a great guy who had left Apple to start an SaaS time clock startup. I fell in love with the idea immediately. And for a little under 3 years now, we’ve been building

This felt very entrepreneurial, as I went a year without pay, I was one of 3 people working on our startup full time in the beginning, I was a part of everything from product to pitching.

But even with my shares in the company, money raised and in the bank, a high six figure salary, and more – something was still missing.

I wasn’t “all in.”

I was all about our startup, but I wasn’t bearing all the risk. It was more like a great startup job.

Babysitting is different than having your own kids.

So this past September, I decided to give birth to my true entrepreneurial spirit. I decided to go all in and launch Visage Payroll, offering free payroll to small businesses and startups.

I walked away from the salary and an awesome startup culture to venture out by myself and build a team, product, and company from scratch — and accumulate a bunch of debt after burning through my savings.

And honestly I couldn’t be happier.

Sure, I’ve got a mortgage, 3 kids (one is 8 weeks old) and a wife. Absolutely, I haven’t made one dime this quarter.

But that’s what “all in” is about, at least for me anyway.

I’m more fulfilled now than I have ever been.

Yes it’s hard.

Of course it’s risky.

But I’ve decided, it’s best for me to be all in and go all out!

(You can follow along with Visage on Twitter, Facebook, and LinkedIn to see what’s in store for Visage in 2015!)

Craig Lewis

Craig is the Founder & CEO at offering Free payroll to startups and small businesses and he's a mega believer of the DFW Startup Community. Craig is also the author of The Sport of Sales His previous startup experience includes launching a sports media and advertising company and prior to Kairos a facial recognition API provider, he launched a traditional payroll company as a subsidiary of a credit card processor ultimately handling $2 billion in transactions. His motto: Think Bigger. Fail Faster. Get Better.